Hydrochloric Acid → 1-{2-[(2S)-2-(Aminomethyl)-4-morpholinyl]ethyl}-7-(methyloxy)-1,5-naphthyridin-2(1H)-one

HRID 657063Notes

Reaction equation

HRID 657063 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:30])[N:10]2[CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][O:18][C@@H:17]([CH2:21][NH:22]C(=O)OC(C)(C)C)[CH2:16]2)=[N:5][CH:4]=1.Cl.O1CCOCC1.C(=O)([O-])[O-]>C(Cl)Cl>[NH2:22][CH2:21][C@@H:17]1[O:18][CH2:19][CH2:20][N:15]([CH2:14][CH2:13][N:10]2[C:11]3[C:6](=[N:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=3)[CH:7]=[CH:8][C:9]2=[O:30])[CH2:16]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 19660Carbonate IonHCID 312751,4-DioxaneHCID 866353461,1-Dimethylethyl [((2S)-4-{2-[7-(methyloxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]ethyl}-2-morpholinyl)methyl]carbamate

Product 1

HCID 689928521-{2-[(2S)-2-(Aminomethyl)-4-morpholinyl]ethyl}-7-(methyloxy)-1,5-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl [((2S)-4-{2-[7-(methyloxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]ethyl}-2-morpholinyl)methyl]carbamate (0.46 g, 1.10 mmol) in CH2Cl2 (10 mL) was added HCl in 1,4-dioxane (1.10 mL, 4.40 mmol) and the resulting solution stirred at ambient temperature for 16 h. After concentration under reduced pressure, the free base was formed by treating with excess MP carbonate to yield a yellow oil. (0.300 g, 85%).

Workup

  1. concentrationAfter concentration under reduced pressure
  2. customthe free base was formed
  3. customto yield a yellow oil

Sources & evidence

ORD record
ord-31fd562301a748d29f5d97c1a6ac90a2
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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